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首页> 外文期刊>Biological chemistry >18O)-labeled singlet oxygen as a tool for mechanistic studies of 8-oxo-7,8-dihydroguanine oxidative damage: detection of spiroiminodihydantoin, imidazolone and oxazolone derivatives.
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18O)-labeled singlet oxygen as a tool for mechanistic studies of 8-oxo-7,8-dihydroguanine oxidative damage: detection of spiroiminodihydantoin, imidazolone and oxazolone derivatives.

机译：18O）标记的单线态氧作为研究8-oxo-7,8-dihydroguanine氧化损伤的机理的工具：检测螺旋藻二氢乙内酰脲，咪唑酮和恶唑酮衍生物。

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摘要

A water-soluble [18O]-labeled endoperoxide derived from N,N'-di(2,3-dihydroxypropyl)-1,4-naphthalene-dipropanamide (DHPN18O2) has been shown to act as a clean chemical source of [18O]-labeled molecular singlet oxygen. This allows the assessment of the singlet oxygen (1O2) reactivity toward biological targets such as DNA. The present work focuses on the qualitative identification of the main 1O2-oxidation products of 8-oxo-7,8-dihydro-2'-deoxyguanosine, which was achieved using high performance liquid chromatography coupled to electrospray ionization tandem mass spectrometry (HPLC-ESI-MS/MS). Thus, the [18O]-labeled and unlabeled imidazolone and oxazolone, together with the diastereoisomeric spiroiminodihydantoin nucleosides, were detected as the main degradation products. In addition, a modified nucleoside that exhibits similar features as those of the oxidized guanidinohydantoin molecule was detected. Our data strongly suggest that the imidazolone and oxazolone nucleosides are generated via the rearrangement of an unstable 5-hydroperoxide intermediate. Interestingly, the combined use of appropriate tools, including isotopically labeled singlet oxygen and the high- resolution HPLC-ESI-MS/MS technique, has allowed to shed new light on the 1O2-mediated oxidation reactions of guanine DNA components.
机译：N，N'-二（2,3-二羟丙基）-1,4-萘二丙酰胺（DHPN18O2）衍生的水溶性[18O]标记内过氧化物已被证明是[18O]的清洁化学来源标记的分子单线态氧。这样可以评估单线态氧（1O2）对生物靶标（例如DNA）的反应性。目前的工作集中在定性鉴定8-oxo-7,8-dihydro-2'-deoxyguanosine的主要1O2氧化产物，这是通过使用高效液相色谱结合电喷雾电离串联质谱（HPLC-ESI）实现的-MS / MS）。因此，检测到[18O]标记和未标记的咪唑酮和恶唑酮，以及非对映异构体spiroiminodihydantoin核苷，作为主要降解产物。另外，还检测到了具有与氧化的胍基乙内酰脲分子相似的特征的修饰的核苷。我们的数据强烈表明，咪唑酮和恶唑酮核苷是通过不稳定的5-氢过氧化物中间体的重排产生的。有趣的是，包括同位素标记的单线态氧和高分辨率HPLC-ESI-MS / MS技术在内的适当工具的结合使用，为鸟嘌呤DNA组分的1O2介导的氧化反应提供了新的思路。

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